


He Likes Skirts, Right?

by crywolf



Category: Homestuck
Genre: Anal Sex, Crossdressing, Crossdressing Kink, Fingerfucking, Lingerie, M/M
Language: English
Status: Completed
Published: 2013-09-21
Updated: 2013-09-21
Packaged: 2017-12-27 05:05:42
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings, Underage
Chapters: 1
Words: 3,881
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/974665
Author URL: https://archiveofourown.org/users/crywolf/pseuds/crywolf
Summary: <blockquote class="userstuff">
              <p>John has a plan. It just so happens that this plan involves wearing a seifuku and ends with Bro swooning. Or so he hopes.</p>
            </blockquote>





	He Likes Skirts, Right?

**Author's Note:**

> I couldn't think of a good title that wasn't cheesy as hell so my friend named it for me.
> 
> The original title was "Seifuck Me". Which is exactly why I shouldn't be allowed to title things.
> 
>  
> 
> I wrote this for Mono and because she's the best, she drew this really great art!  
> http://monoscribbles.tumblr.com/post/62304327888/nsfw-brojohn-with-a-seifuku-under-the-cut

Your name is John Egbert and the opportunity you have been waiting for has finally presented itself. You are spending the weekend at your best friend's apartment. An apartment he shares with his brother, Bro Strider. A very important bit of information, you'd say. And because of unforeseen circumstances, Dave has accidentally double booked himself. He invited you over forgetting he had already taken a shift at the record store (more of a hipster douche hangout complete with attached coffee shop) this Saturday evening. This Saturday meaning _tonight_. He'd be out til late as well - the shop turned into a sort of indie open mic on the weekends. This means it was just you and Bro tonight. And you had some plans.

You've had a crush on Bro Strider ever since the first time you met the guy. That was back when you were thirteen and still lived in Washington. Since then, you had moved to Texas. It was due to a promotion you father had received. He was given several locations to choose from, but when you'd found out that Houston was one of them, you'd practically begged your dad to let you move closer to your best bro. Because he was the greatest parent in the world, it hadn't taken much convincing.

During your first stay in the Strider household, you'd barely managed to say more than a few words to Bro. He was intimidating to say the least. You weren't very subtle about your infatuation either, which made things more embarrassing. You blushed furiously if he even stood in the same room as you, and you lost the ability to form words when he spoke to you directly. Things were different now, though. Maybe not by much, since you still went all red when he looked your way, but your brain had finally stopped turning to mush every time you saw him.

You're sixteen now and you've been harboring a school girl crush on Bro for roughly three years. It was time to make a move. You were going to make this happen. Your plan was basically fool proof. If your assumptions were correct, that was. You knew Bro was a pretty weird guy, judging by his profession and his overall appearance, so you hoped this worked. If not, you were about to embarrass yourself beyond belief. But Dave had mentioned something about "Bro's weird fetish" and you hoped he was serious.

At the moment, you were sitting in Dave's room. He'd left about a half an hour ago and his shift should be starting right about now. The apartment was empty, apart from you and Bro, who was relaxing on the futon in the living room. It was now or never.

You take a deep breath and pull the pink plastic bag out of your backpack. Inside there's a short, pleated skirt, a white top with a neck tie, high socks, a pair of black flats, and a pair of lacy panties to match. Fuck, you were really doing this. You shed your normal clothes, down to your Ghostbusters underwear, all the while convincing yourself this was a terrible idea and you should stop. But you've come too far now.

You trade your boxers for the panties, and take a minute to admire them. You had to admit they were pretty cute. They definitely weren't as comfortable as boxers, but they made you feel confident. You pull on the skirt, zipping it up at the side, and then slide the shirt over your head. Once you have the socks and shoes on, your uniform complete, you regard yourself in Dave's full length mirror. You were 100% anime school girl. Bro had said something about you having anime eyes once, and as you bat your eyelashes at your own reflection, you have to agree. You were starting to feel like this might work!

That doesn't stop your hands from trembling as you reach for the knob of Dave's door, though. You suck in a breath and open it.

Bro is still facing the tv as you enter the room. You walk over to the couch and suddenly feel extremely awkward. You hadn't thought this out very well, because you were now at a loss for what to do. Shit.

"Hey, Bro." You say from behind him. He doesn't turn to look, giving you a mumble in place of a real greeting. He hasn't seen you yet, still a chance to turn back now and he'll never be the wiser - You frown. No, you are doing this. You've been in love with him for too long and you can't bear not knowing how he feels about you. Did you say love? You meant like a lot. Yeah. Right. Okay, just get on with it already.

Putting your hands on your hips, you move around the couch and stand in his view, blocking the tv.

"I _said_ , 'hey, Bro.'" You repeat. He's staring at you now and you feel your heart rate speed up. Oh, god, he's just staring at you with his dumb poker face, oh god oh god, what is he thinking? You can't tell because his eyes are still hidden behind those stupid, idiotic, anime shades of his and you have the sudden urge to run. Run and hide and never come out because _he's just staring at you._

After a few seconds - minutes, hours, you really can't tell - he finally moves. His hand comes up to his glasses and he pushes them up, revealing those bright orange eyes you'd only ever caught brief glimpses of. They were now focused on you, wide with surprise. You really hoped it was the good kind of surprised.

"Egbert?" He says, breaking the silence.

Your hands drop to your sides, losing the confidence you had before. Your hands are still shaking and you can't breathe anymore, you just want to get out of there because you're sure he's going to start laughing any second. Why did you think this was a good idea?

"Fuck, I'm just going to-" You move to leave but he catches the fabric of your skirt before you can. You stop where you are and look back at him. His expression has softened a bit, but it's still shocked.

"No, wait," He says, pulling you back over. You watch him uncertainly as he lifts his other hand to your thigh and pulls you closer. The corner of his mouth twitches in what you guess must be amusement. "Are you... trying to seduce me?"

Oh no, he's definitely laughing at you. He's going to tease you and never let you live this down because you are _so stupid_. Of course he doesn't like you that way, you're just his little bro's awkward, skinny, teenage friend. And on top of that you were now wearing a seifuku in his living room. What the fuck is wrong with you? You cover your face with your hands as your face flushes even more.

"Oh my god, just- just forget this ever happened." You plead, trying to pull away from his grasp.

"Why would I want to forget this?" Bro asks, his grip on your thigh tightening. You peak through your fingers to see his smile widening. "Not when you look so cute."

"Please, just let me go die in a hole now." You groan, hiding your eyes again. Abscond. Abscond _now_.

But you can't do that. Bro is holding you in place, waiting for you to literally keel over and die of embarrassment.

" _Please_." You're practically begging, and not in the way you had hoped. You'd wanted this to go very differently. In your mind, Bro scooped you up into a kiss, unable to control himself, maybe carrying you to his bedroom and taking you in a manly fashion. Instead you have Bro practically laughing at you. Because this is real life and not a fantasy.

He lets go of your skirt and you feel relief rush through your body. It's short lived, though, because next thing you know his hands are on your wrists and pulling them away to uncover your face.

"Christ, kid." Bro breathes, his face more serious now. "You can't just waltz in here looking like that and then get all shy and change your mind."

You watch him with a confused expression. "W-what?"

His response to that is to drag you into his lap and run his hands up the back of you bare thighs. _Holy shit_.

"You've been teasing me long enough." He says, breath hot on the skin of your neck. You feel a shiver run down your spine. "Batting those anime eyes at me... fuck, it's enough to drive a guy crazy."

Wait, hold on. Teasing him?

"You mean-"

You don't get to finish that thought because his lips are crashing against yours. You're not prepared for it and your teeth get in the way, clacking awkwardly against Bro's. He ignores the unpleasant jarring sensation and starts to suck and nibble on your lips, his hands moving up your skirt and grabbing your ass. You let out a surprised squeak, reflexively pulling back. He takes this opportunity to move to your throat to suck and bite there.

"I've been trying to read your fucking mixed signals for ages. It's like trying to decipher some seriously encrypted Russian radio waves or some shit." He drags his tongue across your skin from your collarbone to just below you ear, then ghosting a breath over it and leaving the wet skin to chill. "You kept me waiting, and I am not a patient man." He punctuates that sentence by grabbing your hips and grinding you against his thigh. You let out a small whimper and he smiles against your neck.

"Well, I- uh... hope this clears things up." You answer, looking down at your outfit shyly and playing with the hem of your shirt. You look back up to his face to find his eyes tracing your body. He licks his lips and when you subconsciously lick yours as well, his eyes flick up to meet yours.

"I hope you know what you've gotten yourself into, kid." He practically growls, his smile predatory. It makes your stomach flip.

"Why don't you show me?" You challenge. Apparently this was the right thing to say because the next thing you know he's standing up and wrapping your legs around his waist. His mouth is on yours again, kissing you deeply. Your arms move around his neck automatically and you tilt your head to ease into the kiss.

You don't remember Bro carrying you down the hallway to his bedroom, but when you open your eyes after being tossed onto the soft sheets, you assume he flash-stepped here. Your head spins for a moment before you get a grasp on reality again. Bro is kneeling above you, pulling his shirt over his head and _wow_ , he's even more toned and sexy than you imagined underneath that tacky polo.

"This is your last chance. If you want out, say so now." Bro says, tossing his shirt aside. You respond by looking up at him with your wide, blue eyes and spreading you legs a little more to flash him your panties. There's a hungry look in his eye before he comes down, pressing your chests together and all but devouring you.

You try to speak but Bro's insistent kissing makes it hard for you to do much more than gasp out a few words. "B-Bro... I - I want... I want, hnnn-" You forget what you were trying to say because suddenly Bro's fingers are playing with the lace lining of you underwear.

"Hmm?" He coos into your ear. "Tell me what you want, John."

Hearing Bro say your name like that, low and intimate, sends a wave of heat through your body. "I want..." You pant, writhing underneath him. He's not moving, though. He's patiently waiting for you to tell him. You're becoming more flustered and frustrated as he keeps his hands on the bed on either side of you. You wanted them running down your sides and touching your skin... "I want you to fuck me."

Bro sits up a bit more and you whine at the lack of contact. He furrows his brow at you. "Whoa, kid, you ever done this before? There's a lot of prep that goes into that kind of thing."

"No," You answer. You had never done anything like this. It was your first time, yeah, but you weren't stupid. "It's okay, though. I - uh... did it myself." You tell him, averting your eyes.

"What do you mean, you did it yourself?" Bro says, smirking. You know he knows what you meant, he just likes watching you squirm.

"I... fingered myself, okay?" It's uncomfortable to say out loud but you want his body against yours again and you don't want to wait any longer.

"Good boy." He hums, moving between your legs to roll his hips against you. He's hard and you can feel the prominent bulge through his jeans. You expect him to do it again, but instead he's kissing his way down your body, lifting your shirt to access the warm skin of your chest and stomach. He goes lower and lower, flipping your skirt up and placing his hands are under your knees, holding them apart. You take a sharp breath when he mouths your hard cock through the satiny material.

"Take them off." You tell Bro. He looks up at you, eyes blazing. It's enough to make you melt into a puddle right there.

"Ask me nicely." He replied, leaning over to lick your inner thigh.

"Please, Bro." You mewl. You're painfully hard and you don't even mind begging at this point. "Please."

He kisses your knee to praise you. "Much better." His breath is suddenly tickling your stomach and you feel his teeth pulling your panties halfway down your thighs, exposing you completely. He hooks his fingers on them and yanks them down the rest of the way. On his way back up, he presses a kiss to the side of your throbbing dick, humming appreciatively.

"Your turn," You mumble, when you're finally face-to-face again. You grasp for his belt and unbuckle it with shaking hands. He grabs your hands and moves them around his neck instead, pulling the belt out of the loops himself. You don't argue. He's much quicker than you would have been and in a few seconds he's shimmied out of his jeans. 

That's when it hits you. Bro Strider mostly naked and on top of you and this most definitely isn't a wet dream. You've had enough of those to be able to tell them apart from the real thing.

Bro brushes your hair off your forehead, leaving a kiss there before leaning away. He reaches into his bedside table to grab a bottle of lube and a condom and then settles back down and pulls you onto his lap.

"Do you really need that?" You ask, frowning at the condom and resting your hands on his shoulders.

"Safety first." He tells you, putting it down on the bed. He takes the lube a rolls it in his hands for a moment. When it's no longer cold, he pours some onto his fingers and rubs it around a bit. "Ready?" You nod and he positions his hand beneath you, pressing one finger to your entrance. You're still a little tense from the nervousness and he must feel it because he moves his free hand to your face. "Come on, babe. Relax for me."

You exhale shakily, loosening you body as much as you can. His finger pushes into you and you concentrate on keeping your body relaxed. He eases in gently, kissing your neck soothingly when you tense up again. When he's in as far as he can go, he gives you a minute to adjust to the pressure. You relax your body again and only get a few breaths out before he curls his finger and your breathing turns into a moan.

"Mmm, I love the sounds you make." Bro purrs, curling his finger once more before he starts to move it. It's not long before you're comfortable enough with the one finger and you're ready for more.

"Come on," you groan, gripping his shoulder tightly. "Another one. I want _more_." He's happy to oblige, pressing another finger inside, prompting more sounds from you.

Soon enough he's got four fingers in and you're rocking against them. It feels amazing but you can't take much more. You need to stop him before you cum. "Bro... Bro..." You whine, patting the side of his face.

"Yeah?" He asks, watching you with a smile and squeezing your hip.

"I want you to fuck me now."

He lets out a breathy laugh and pulls his fingers out. "But you look so pretty like this." He kisses you open mouth and flicks his tongue across your bottom lip. You're getting impatient so you bite his lip and reach under the waistband of his underwear to grab his cock. He's just as hard as you are and you can feel the precum making him slick. You give him a few pumps and he makes a few appreciative sounds.

He picks you up and lays you on your back. "Damn, you're persuasive." He takes the condom again and you stop him before he can unwrap it.

"Do we have to?" You ask. He frowns at you. "I mean, you're clean, aren't you?"

"Well, yes, but-"

"Then we don't need it. It's my first time and... I want to be able to _feel_ you."

Bro's breath hitches and you know you're going to get your way. You take the package from his hand and toss it to the floor.

"Shit, John..." He growls, dragging your hips closer, spreading you open more. He takes lube again and squirts a generous amount onto his prick. He stokes it a few times before positioning himself against your entrance. He slowly pushes in and, wow, he's really big and it's uncomfortable.

"Fuck, you're so tight," Bro gasps as he presses in more. You can feel tears pricking at the corner of your eyes as you bite your lip. Bro rests his hands on the bed on either side of you and the mattress dips. You're still gripping his shoulders - there are probably red marks on his skin from your nails - as he pushes in the rest of the way until he's filling you completely. Your breath is coming short and you feel stretched to your limit, but god, it hurts in the best way possible.

After a minute, once you've composed yourself and have adjusted to his size, you speak. "Bro, you c- can move now..."

Bro grunts in response, and lifts a hand to your face to wipe away the tears that spilled down your cheeks. He smiles and slowly pulls out most of the way and then pushes back in quickly. You're caught a little off guard and has you making a strangled sound. He continues at a slow pace and as you loosen up, the pain subsides and the pleasure intensifies.

"Faster," You whimper, clinging to his shoulders. " _Harder_."

He takes your instruction and starts thrusting faster. Your swollen cock rubs against his stomach, but his smooth skin doesn't give you the friction your body is aching for. But you almost forget about it when you feel a sudden burst of pleasure as he hits your sweet spot.

"Ah!" You're loud and you really don't care who hears because the face Bro makes when he hears you is just too satisfying. He keeps going though, pounding into you, sending more waves of pleasure through you. His arms are hitting against the back of your knees and he's panting hot breaths onto you. You slip one of your hands from his shoulder and reach down to grab your neglected dick, giving it the attention it needs. Bro sees this and pushes your hand away, replacing it with his own.

"Let me." He says, fucking you slowly and stroking you at the same frustratingly slow pace. You're desperately writhing and whining as he smirks, enjoying the show you're putting on for him.

"Bro." You're almost crying again.

"Say it again." He orders. "Say my name."

You do. You're pretty sure it's the only word left in your vocabulary right now. " _Bro_."

He starts thrusting into you faster, jacking you off while he does so. You can feel yourself getting close to the edge, a warm feeling gathering low in your belly and spreading through your body. You moan, screwing your eyes shut. "I'm gon- I'm gonna..."

"Come for me." His voice is breathy and his motions are becoming less controlled, and you buck against him just a frantically. He hits your prostate just right a few more times and oh god, the heat is rising through you and you gasp. 

"Bro!" You cry, seeing stars and coming onto his stomach and your skirt. Your body is tensing around Bro's cock and he works you through your orgasm. The hand that's not gripping you moves to your hip. His fingers dig into your skin as he hold you in place, continuously pounding into you and a few seconds later he follows, spilling into you with a shuddering moan.

Once you've both caught your breath, Bro pulls out and the loss of pressure feel weird, and so does the feeling of the warm liquid sliding out of you. You ignore it, though, because he's kissing you again.

"You got your outfit all dirty." He tsks, dragging his finger through the cum on your skirt. "What a shame." He brings the finger up to his lips and suck on it thoughtfully. Your breath hitches and your now softening dick twitches with interest. "Mm. You taste as good as you look."

You're unsure what to do now. Bro is watching you with half-lidded eyes and you're tired and blissed out, but maybe you're supposed to leave? You don't want to, but you've never done this before and don't know if there's some sort of post-fucking protocol...

Bro lays down next to you and pulls you into his arms, answering your question. You relax against him and your legs intertwine automatically. He pushes the hair out of your eyes and presses a kiss to the top of your head.

"This isn't going to be a one time thing, is it?" Bro asks, and this time it's his turn to sound uncertain. "Because I don't want it to be."

Bro sounds different. He's talking to you like you're... you. And not just his little brother's friend. You like it.

"Hell, no." You answer, snuggling into his chest, not caring that he's a little sweaty and that you're both in serious need of a shower. "Sorry, but you're sort of stuck with me now."

He chuckles and you enjoy the way it shakes your body. "Fine by me."

You end up falling asleep like that, wrapped in Bro's arms, listening to his breathing slow. You vaguely remember that Dave will be coming home in a few hours, but you can't bring yourself to care. At this moment, everything is perfect.


End file.
